The Hottest Towns and Neighborhoods for Every Generation

A 2020 guide to the best Greater Boston towns and neighborhoods for every generation—from Millennials, to Gen Xers, to Boomers.

A new-construction home in Sudbury, which offers families plenty of room to spread out. / Photo by Greg Premru; Architecture by LDa Architecture & Interiors



2019 Median Home Price: $640,932
One-Year Change: -1%
Commute Time: 1h 14m*

You might know Acton for its A-plus public education system—it scored second place in Boston’s 2019 ranking of top high schools—but after the bell rings, the town doesn’t turn into a sleepy suburb. Real estate agents are increasingly pointing younger buyers toward West Acton, where Colonials and spacious yards mingle with a buzzy new fair-trade coffee shop, a craft brewery, and a barre studio. Itching for some fresh air? Hop onto the area’s recently expanded rail trail or bike to neighboring Concord, where you can enjoy the quaint downtown without paying the high prices to live there.

Gen X

2019 Median Home Price: $863,292
One-Year Change: 15%
Commute Time: 1h 5m

If you’re looking for a couple thousand square feet plus a couple of acres for the kids and dog to frolic on, you’ll find it in Sudbury, where an abundance of new and antique builds makes it easy to find your forever home. “I often find that when folks are house-hunting in Weston and Wayland, they usually end up landing here because you can buy more for your money,” says Sudbury-based Gibson Sotheby’s agent Elise Siebert. Bonus points for the kid-friendly Sky Bar candy factory and the sparkling new Whole Foods, where shoppers may soon be able to sip a glass of wine while browsing the aisles.


Chestnut Hill
2019 Median Home Price: $1,660,000
One-Year Change: 26%
Commute Time: 30m

For seasoned buyers who’ve put in their time raking leaves and shoveling snow, Chestnut Hill is increasingly offering the chance to delegate the grunt work and simply enjoy retired living. In addition to plenty of existing condo complexes, “We’re seeing an increase in converted two-family homes that offer the luxury of new construction with the ease of condo living,” says local Compass agent Allison Blank. Nearby high-end shopping and dining, meanwhile, make it easy to treat the grandkids. “There’s a discerning consumer here who wants it all and isn’t willing to compromise,” says Alana Stein, general manager of the Street.

Indie boutiques and restaurants steps from the water? There’s no place like Newburyport. / Photo by Walter Bibikow/Getty Images



2019 Median Home Price: $612,852
One-Year Change: 31%
Commute Time: 1h 9m

Arts, culture, craft beer, and beaches—it’s good to be a young Beverly resident. Beyond the nano-breweries and hip new restaurants (see: legendary chef Frank McClelland’s new farm-to-table spot) popping up on every corner, there’s also a wealth of apartment buildings rising around Beverly Depot, one of five commuter-rail stations in town. And with the local nonprofit Beverly Main Streets recently launching its plan to continue transforming the up-and-coming downtown over the next decade, first-time homebuyers have the chance to build their community as it gets built up around them.

Gen X

2019 Median Home Price: $899,628
One-Year Change: 30%
Commute Time: 1h

Don’t be surprised if the Discover Marblehead committee officially welcomes you to town with a “newcomer box”: This small North Shore enclave is all about neighborliness. And with several beaches to hang out on after school lets out, the kiddos will surely feel welcome, too. As for housing, families looking to trade up can treasure-hunt among characterful single-families dating to the 18th century along the cobbled streets of Old Town, while those who need a little less space will appreciate the newer condo complexes around Marblehead Neck’s yacht clubs.


2019 Median Home Price: $772,033
One-Year Change: 26%
Commute Time: 1h 12m

With the 65-plus crowd making up 20 percent of Newburyport’s population, it’s not hard to find good company with which to enjoy the waterfront concert series in the summer, the harvest festival in the fall, and the boutique shopping and boardwalk all year long. “We have a huge influx of people in their fifties and sixties looking for that ‘sidewalk’ style of living,” says Jamie Dee Frontiero, a local Coldwell Banker agent who says the town’s relatively small plots clustered within walking distance of downtown tend to appeal to empty nesters. “They want to leave their home and be in town within a few blocks of their doorsteps.”

The newly revitalized downtown is just one reason young homebuyers are flocking to Quincy. / Photo by DenisTangneyJr/Getty Images



2019 Median Home Price: $551,832
One-Year Change: 12%
Commute Time: 33m

A single-family home that’s walking distance to the T and the beach for around $500,000? No, it’s not a scam or a real estate fever dream—it’s a reality in Quincy. But it’s not just relative affordability and proximity to Boston that makes the city a hot buy. Landmark Property Group Realtor Pete Guiney credits the revitalization of Quincy Center, where shiny new condo and apartment buildings mingle with a thriving restaurant scene, for attracting the next generation of homeowners. “In a short amount of time,” he says, “Quincy has become a hip spot to live and go out at night.”

Gen X

2019 Median Home Price: $1,012,007
One-Year Change: 23%
Commute Time: 44m

You know you live in a family-friendly town when nearly every holiday—from July Fourth to Christmas—is celebrated with a parade or a festival. But beyond cherished town-wide traditions, local Coldwell Banker agent Tara Coveney says Hingham’s walkable downtown and well-regarded schools have recently made the harborfront town popular with buyers ready to graduate from city living. “The amenities make the transition from Boston to the ’burbs less daunting,” she says. It doesn’t hurt that locals can hop onto the MBTA ferry and make it back downtown in just 40 minutes.


2019 Median Home Price: $909,964
One-Year Change: 34%
Commute Time: 52m

Duxbury is like the Cape without the crowds—and that, says Waterfront Realty Group sales agent Kelsey Berman, is exactly what local baby boomers are looking for. “We have a lot of demand from people looking to downsize,” she says. While some golden-agers gravitate toward the beachy town’s Capes and ranches with first-floor master bedrooms, others find worry-free living at one of several condo complexes, such as Ocean Woods and Bay Farm. All enjoy Duxbury’s buzzy amenities, from Island Creek Oyster Farm’s breezy patio to Millbrook Station’s indie boutiques.

Roomy row houses make Charlestown a family-friendly choice in the city. / Photo by DenisTangneyJr/iStock



2019 Median Condo Price: $519,495
One-Year Change: 7%
Commute Time: 24m

Boston’s largest neighborhood is packed with up-and-coming nooks and crannies, from the new housing and shops electrifying South Bay Center to the massive mixed-use development, dubbed the Beat, under construction in Savin Hill. For first-time buyers, though, agents say much of the action centers around Lower Mills, where residents can commute to the Red Line on a vintage trolley, bike along scenic trails in the Neponset River Reservation, and still score a condo in a renovated triple-decker for around $500,000.

Gen X

2019 Median Condo Price: $764,325
One-Year Change: 5%
Commute Time: 17m

For those with a few kids but no desire to pack up for the ’burbs, Charlestown offers the best of both worlds: roomy, family-friendly rowhouses on gas-lamp-lit streets (at a relatively reasonable price per square foot, no less)—all just a 10-minute T ride to the North End. A proposed new ferry route, meanwhile, could soon link Charlestown to East Boston, the Seaport, and downtown, making it one of the most connected spots around. In other words: Get in while you still can.


2019 Median Condo Price: $2,029,508
One-Year Change: 69%
Commute Time: 7m

It’s a lot easier to stomach downsizing when the facilities at your new pad include an indoor golf simulator or a wine-tasting room. That’s what empty nesters will find inside the Seaport’s growing collection of residential towers. The perks continue outside: In 2020 alone, the waterfront district is slated to add another 700,000 square feet of amenity space, according to Todd Norley, VP of leasing at WS Development. “We repeatedly hear that the sense of community this neighborhood offers brings joy and new life experiences,” he says.

*Commute times to the Financial District were sampled during morning rush hour in February. 

Read more about top places to live in Boston in 2020.

A previous version of this story misidentified the number of commuter-rail stations in Beverly as well as the type of housing being built around Beverly Depot.